An exceptional P-H phosphonite: biphenyl-2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper-catalyzed 1,4-additions

Biphenyl-2,2'-bisfenchol (BIFOL) based chlorophosphite, BIFOP-Cl, exhibits surprisingly high stabilities against hydrolysis as well as hydridic and organometallic nucleophiles. Chloride substitution in BIFOP-Cl proceeds only under drastic conditions. New enantiopure, sterically demanding phosph...

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Published inBeilstein journal of organic chemistry Vol. 1; no. 1; p. 6
Main Authors Kop-Weiershausen, T, Lex, J, Neudörfl, J-M, Goldfuss, B
Format Journal Article
LanguageEnglish
Published Germany BioMed Central Ltd 26.08.2005
Beilstein-Institut
Subjects
asymmetric conjugate additions
biaryls
Chemistry
chirality
Full Research Paper
phosphites
phosphonites
phosphoramidites
phosphorus ligands
X-ray analyses
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Summary:Biphenyl-2,2'-bisfenchol (BIFOL) based chlorophosphite, BIFOP-Cl, exhibits surprisingly high stabilities against hydrolysis as well as hydridic and organometallic nucleophiles. Chloride substitution in BIFOP-Cl proceeds only under drastic conditions. New enantiopure, sterically demanding phosphorus ligands such as a phosphoramidite, a phosphite and a P-H phosphonite (BIFOP-H) are hereby accessible. In enantioselective Cu-catalyzed 1,4-additions of ZnEt2 to 2-cyclohexen-1-one, this P-H phosphonite (yielding 65% ee) exceeds even the corresponding phosphite and phosphoramidite.
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ISSN:1860-5397
1860-5397
DOI:10.1186/1860-5397-1-6